Ammonia → HCID 178519770, compound

HRID 2236542Notes

Reaction equation

HRID 2236542 reaction equation
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([C:10]2[CH:14]=[CH:13][O:12][CH:11]=2)[C:7](=[O:9])[CH:8]=1.[NH3:15]>CO>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([C:10]2[CH:14]=[CH:13][O:12][CH:11]=2)=[CH:5][N:15]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 42625981HCID 42625981, compound

Product 1

HCID 178519770HCID 178519770, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-hydroxymethyl-5-furan-3-yl-pyran-4-one (1.92 g, 10.0 mmole) and 7 M ammonia in methanol (50.0 mL) is stirred and heated in a sealed vessel at 90° C. overnight. The reaction mixture is cooled, evaporated to dryness in-vacuo, taken up in 15% methanol in chloroform and passed thru a pad of magnesol and silica gel eluting with the same solvent. The eluate is evaporated, treated with acetone, filtered, washed with acetone and air dried to give a-grey solid, 1.21 g, (63%); MS (ES+): m/z 192.2 (M+H).

Workup

  1. temperatureThe reaction mixture is cooled
  2. customevaporated to dryness in-vacuo
  3. customThe eluate is evaporated
  4. additiontreated with acetone
  5. filtrationfiltered
  6. washwashed with acetone and air
  7. customdried
  8. customto give a-grey solid, 1.21 g, (63%)

Sources & evidence

ORD record
ord-ccd1789258624bfbbef62b37faf2338d
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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